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Converting $100,000 to a Roth in November Could Sidestep the Jan. 15 Estimated Tax Payment

Original: Convert $100,000 to a Roth in November and Skip the Jan. 15 Payment. If Your Withholding Already Matches Last Year's Tax, the Penalty Is $0. If It Doesn't, It's About $1,000

A tax planning strategy making the rounds suggests converting $100,000 to a Roth IRA in November and skipping the January 15 estimated tax payment. Under safe harbor rules, taxpayers whose withholding already matched last year's tax liability would owe no penalty; those short on withholding would face a penalty of roughly $1,000. It's the kind of year-end maneuver personal finance writers and advisors highlight as the Roth conversion window narrows.

Why now: Year-end tax planning season has people weighing Roth conversions and estimated payment deadlines.

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